6-Phospho-beta-D-glucosyl-(1,4)-D-glucose (ECMDB21504) (M2MDB001899)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-08-09 09:25:10 -0600
Update Date2015-06-03 17:21:40 -0600
Secondary Accession Numbers
  • ECMDB21504
Identification
Name:6-Phospho-beta-D-glucosyl-(1,4)-D-glucose
Description6-phospho-beta-D-glucosyl-(1,4)-D-glucose is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 4-O-(6-O-phosphono-b-D-Glucopyranosyl)-b-D-glucopyranose
  • 4-O-(6-O-Phosphono-beta-D-glucopyranosyl)-beta-D-glucopyranose
  • 4-O-(6-O-phosphono-β-D-Glucopyranosyl)-β-D-glucopyranose
  • 6-O-phosphono-b-D-Glucopyranosyl-(1Right4)-b-D-glucopyranose
  • 6-O-Phosphono-beta-D-glucopyranosyl-(1right4)-beta-D-glucopyranose
  • 6-O-phosphono-β-D-Glucopyranosyl-(1Right4)-β-D-glucopyranose
  • 6-phospho-b-D-Glucosyl-(1,4)-D-glucose
  • 6-Phospho-beta-D-glucosyl-(1,4)-D-glucose
  • 6-phospho-β-D-Glucosyl-(1,4)-D-glucose
  • Cellobiose 6-phosphate
  • Cellobiose 6-phosphoric acid
Chemical Formula:C12H23O14P
Weight:Average: 422.2764
Monoisotopic: 422.082541956
InChI Key:ITPHOIFCAFNCLL-QRZGKKJRSA-N
InChI:InChI=1S/C12H23O14P/c13-1-3-10(7(16)8(17)11(19)24-3)26-12-9(18)6(15)5(14)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-2-yl]methoxyphosphonic acid
SMILES:[H][C@@]1(O)O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(COP(O)(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@]([H])(O)[C@@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentDisaccharide phosphates
Alternative Parents
Substituents
  • Disaccharide phosphate
  • Glycosyl compound
  • O-glycosyl compound
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • 6-phospho-beta-D-glucosyl-(1->4)-D-glucose (CHEBI:2233 )
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility40.7 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.21 m³·mol⁻¹ChemAxon
Polarizability35.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
6-Phospho-beta-D-glucosyl-(1,4)-D-glucose + Water > D-Glucose + Glucose 6-phosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_18) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08n9-0902500000-b67f737a4a61476245c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1900000000-6b9e43fb6a7ba155cce8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-1900000000-23a1f23a5ac78392918eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-9634800000-7dc62f0a531f731360bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-89ae5f03d5f8e22417d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-d86f9a65f1c247ebc70bView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID2233
HMDB IDNot Available
Pubchem Compound ID440376
Kegg IDC04534
ChemSpider ID389331
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 6-phospho-beta-glucosidase BglB
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin and arbutin
Gene Name:
bglB
Uniprot ID:
P11988
Molecular weight:
53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
2. 6-phospho-beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:
chbF
Uniprot ID:
P17411
Molecular weight:
50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
3. 6-phospho-beta-glucosidase AscB
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin, cellobiose, and probably arbutin
Gene Name:
ascB
Uniprot ID:
P24240
Molecular weight:
53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
Protein Details
4. 6-phospho-beta-glucosidase BglA
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
Gene Name:
bglA
Uniprot ID:
Q46829
Molecular weight:
55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.